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Point Me To First Class — Places & Travel
Point Me To First Class

Point Me to First Class is a show for employed professionals, solopreneurs, entrepreneurs, and business owners with higher-than-average personal and/or business expenses who want to learn to leverage them into credit card points to spend on travel. Your expenses are your greatest untapped asset – but learning how to use them to travel the world doesn’t have to be confusing or complicated.

Each week, Devon Gimbel shares valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points and shows you how to spend them on incredible travel experiences.

Interested in learning more about working with Devon? Visit www.pointmetofirstclass.com to learn more.

This podcast is for you if you find yourself asking questions like:
How do I earn credit card points and use them for travel?
How can I make my expenses benefit me?
How can I earn as many credit card points for as little spending as possible?
How to maximize value from credit card points.
How to earn credit card points for travel.
Turn credit card points into travel.

Copyright: © 2024 Devon Gimbel MD LLC All Rights Reserved

Latest Episodes:

148. Your Year in Points Review: How to Audit, Learn, and Plan Smarter Dec 29, 2025

Show notes

Have you ever taken a step back and actually evaluated what your points did for you over an entire year?

In this episode, I'm inviting you to do your own Year in Points Review—a way to look at how you earned points, how you used them, and whether your approach to earning and redeeming rewards helped you reach your travel goals.

I walk through why a year-end points review is worth doing, including how it helps you evaluate what you did well, what you could do better, and how having clear data makes it easier to decide what to keep doing, what to stop doing, and what to focus on moving forward.

I also share my personal process for reviewing both sides of the equation: points earning and points redeeming. From looking at different points ecosystems to understanding how points were earned and used, this episode walks through how to pull the details of the year into a clearer big picture.

If you want to better understand how your points worked for you this year, this episode will show you how to get started.

Get full show notes and transcript: https://pointmetofirstclass.com/year-in-points-review-2025

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

147. 2025 in Points and Miles In Review (Part 2): Key Changes, New Realities, and What Comes Next Dec 22, 2025

Show notes

What really changed in the points and miles world this year—and how should that shape your strategy going forward?

In part two of our 2025 Year in Review, Kelly and I continue breaking down one of the most transformative years we've seen in award travel. Beyond rising annual fees and tightening loyalty programs, this year revealed deeper structural shifts in how airlines price awards, who gets access to the best redemptions, and what flexibility actually looks like going forward.

We dig into the continued expansion of dynamic pricing—and why it isn't always the disaster it's made out to be. You'll hear real examples of when dynamic pricing has increased access and value, along with why moments of program change can sometimes be the best time to book.

We also explore how airlines are reshaping award access around status and cardholder loyalty in ways that go far beyond free bags or early boarding. For the first time, elite status and co-branded cards are directly impacting award availability, pricing, and even whether certain premium cabins can be booked at all.

We wrap it all up by zooming out to talk about what all of this means for 2026 and beyond—how transferable points are evolving, why diversification matters more than ever, and how to think strategically about status in a landscape that's clearly shifting.

If you enjoyed part one of our year in review, this conversation brings the full picture into focus.

Get full show notes and transcript: https://pointmetofirstclass.com/2025-points-miles-year-in-review-part-2/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

146. 2025 in Points and Miles In Review: The Biggest Wins, Disappointments & Shifts - Part 1 Dec 15, 2025

Show notes

In this episode, we bid farewell to 2025 with a year-in-review analysis of the biggest news, changes, and trends in rewards, credit cards, and award travel over the last 12 months.

This episode is part one of a two-part year-in-review series, and I'm joined by Kelly, the Points and Miles Doc, to break down the biggest changes, surprises, and shakeups in the points and award travel world over the last year.

In this first half of the conversation, we focus on the biggest wins and disappointments of the year—from credit card issuers that made significant changes to new programs that expanded what's possible with points. We talk through how the landscape has shifted, why earning and redeeming points feels more complex than it used to, and how those changes showed up across credit cards, transferable points currencies, and airline loyalty programs.

This episode isn't about declaring whether 2025 was "good" or "bad." It's about understanding how the points and miles world is becoming more specific, more nuanced, and more complex—and what that means for how you participate in it moving forward.

Be sure to tune in next week for Part Two, where we'll dive deeper into the trends we expect to shape 2026, along with our predictions and award travel wish lists for the year ahead.

Get full show notes and transcript: https://pointmetofirstclass.com/2025-points-and-miles-year-in-review-part-1/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

145. Behind the Scenes at World of Hyatt: Loyalty, Care & the Future of Travel with Laurie Blair Dec 08, 2025

Show notes

Have you ever wondered what exactly goes on behind the scenes in loyalty programs—and what drives executive decisions about what to offer, add, or take away from their members' experience?

In this episode, I get to do exactly that. I'm joined by Laurie Blair, Hyatt's Senior Vice President of Global Marketing and Loyalty, for a rare behind-the-scenes look at how Hyatt designs a program that travelers actually feel loyal to.

We talk about what truly sets the World of Hyatt program apart, how they make decisions about elite benefits and redemptions, and what status holders can expect in the future. We get into everything from the rarity of fixed award charts and hotel loyalty programs, stealth devaluations, and Hyatt's approach to balancing business goals with prioritizing their members—to the underrated redemptions you should absolutely be taking advantage of.

Laurie also shares what it's like to build a loyalty program that discerning travelers trust and love, how Hyatt listens to its members, and why care—not just points—is the foundation of everything they do.

If you've ever wondered how loyalty is built inside one of the most respected travel brands in the world, this is your backstage pass.

Get full show notes and transcript: https://pointmetofirstclass.com/world-of-hyatt-behind-the-scenes/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! https://docs.google.com/forms/d/e/1FAIpQLSeAPfb3wIaphMn_NoQzm_fljydsivTELQwh7pYoxrI2uTFoKQ/viewform?usp=header

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

144. Inside Rove: The Loyalty Program Reshaping Points & Miles Dec 01, 2025

Show notes

There's a new player in the rewards space, and it's changing what's possible for earning points even if you never open another credit card.

In this episode, I'm joined by Carissa Rawson, Director of Travel and Marketing for Rove, a fast-growing loyalty platform that combines a travel booking portal with an online shopping portal so you can earn transferable miles on hotel stays, flights, and everyday purchases.

Whether you're new to points or you've been in the hobby for years, Rove offers earning opportunities that can work for everyone. Carissa and I talk about how the platform works, how you can use the miles you earn, and why Rove can stack with the cards and programs you already use. We also get into some of the most eye-catching multipliers currently available—like hotel bookings offering 25x, 40x, or even 55x miles.

You'll hear how loyalty-eligible hotel rates work, how Rove handles posting timelines for both travel and shopping, and what to expect from their customer support. We also cover Rove's transfer partners, including newly added and exclusive options, and how members can redeem miles for flights or hotels. Tune in to hear the most common mistakes new users make, upcoming features on the horizon, and special bonuses available for listeners. *****

Special bonus for PMTFC podcast listeners! New to Rove? Sign up now and receive 1,500 Rove miles automatically at www.rovemiles.com/pmtfc

*****

Turn your expenses into points and save tens of thousands of dollars a year on your wishlist travel. Don't miss out! Click here to know more about my comprehensive online program, Points Made Easy.

Get full show notes and transcript: https://pointmetofirstclass.com/rove-loyalty-platform/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! https://docs.google.com/forms/d/e/1FAIpQLSeAPfb3wIaphMn_NoQzm_fljydsivTELQwh7pYoxrI2uTFoKQ/viewform?usp=header

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

143. Your Holiday Points Prep Checklist: 5 Steps to Maximize Seasonal Spending Nov 24, 2025

Show notes

This week marks the biggest points-earning opportunity of the entire year—especially if you're planning to shop online. While everyone else is focused on Thanksgiving prep, points and miles travelers know this is the week to turn everyday purchases into tens of thousands (or more) of bonus points.

In this short and focused episode, I'm sharing my 5-step points-earning prep checklist for holiday spend—the exact steps I complete before, during, and after the holiday shopping surge to stay organized, stay strategic, and maximize every earning opportunity.

We'll cover how to identify what to purchase ahead of time, how to choose which rewards cards to use based on your earning goals or spend-related bonuses, how to set up the shopping portals and tools that streamline your holiday purchases, and the simple steps that help ensure your bonus points track correctly.

This checklist walks you through what to do before, during, and after your holiday shopping so you can maximize the points you earn while keeping the process as stress-free as possible.

Get full show notes and transcript: https://pointmetofirstclass.com/holiday-points-earning-checklist/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

142. How Points Become a Tool for Freedom, Joy & the Life You Want to Live with Dielle Charon Nov 17, 2025

Show notes

Travel is never just about the destination — it's about what the journey makes possible.

In today's episode, we explore how learning to earn and use credit card points isn't just a smart financial decision. It's a pathway to freedom, abundance, and experiences that reflect the life you actually want to live. From upgraded flights to dream hotels, points can turn everyday expenses into extraordinary opportunities.

No one embodies that transformation quite like Dielle Charon. A former social worker turned seven-figure business coach for women of color entrepreneurs, Dielle has used points not only to change the way she travels, but to expand what she believes she deserves.

In this conversation, we explore Dielle's shift from a scarcity mindset around money and travel to one grounded in abundance. We talk about the emotional impact of flying business class for the first time, how points became a tool for self-care, celebration, and access, and why choosing ease and luxury can be deeply supportive — not frivolous.

Whether you run a business or simply want to travel with more intention and possibility, this episode offers a powerful look at what becomes available when you allow points to elevate more than just your travel plans.

This conversation is rich with honesty, strategy, and inspiration — and it's about so much more than travel. It's about possibility, mindset, and unapologetically claiming ease, luxury, and joy.

Get full show notes and transcript: https://pointmetofirstclass.com/points-abundance-mindset/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

141. Listener Q&A: Canceling Cards, Transfer Partner Confusion & Shopping Portals vs. Welcome Bonuses Nov 10, 2025

Show notes

This episode is all about your questions—and real answers. I'm back with another listener Q&A, tackling the points and miles decisions you're actually making right now.

From whether it's possible to move points between airline partners to deciding if that old United card still deserves a spot in your wallet, we're covering it all.

We'll walk through when to hold or cancel airline cards, how to decide between co-branded and transferable points programs based on your travel goals, and how to decide which airline booking program is best when you have multiple options to book award flights.. You'll also hear my take on shopping portals, welcome bonuses, and the Mesa card.

This episode is packed with strategy, frameworks, and real-world examples to help you make confident decisions and earn more value from every point.

Turn your everyday expenses into travel—and learn how to build a points strategy that actually works for you.

Get full show notes and transcript: https://pointmetofirstclass.com/maximize-points-and-miles-travel-strategy/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here

140. Points Path: The Tool That Shows You the Best Value for Every Flight Nov 03, 2025

Show notes

Ever look at Google Flights and wonder, "Should I use points for this or just pay cash?"

If you've ever felt unsure about which option gives you the best value, this episode is for you.

In the final episode of our Streamline, Stack, and Save mini-series, I'm joined by Julian Kheel, former editorial director at The Points Guy and senior editor at CNN, now founder of Points Path — a browser extension that works seamlessly within your browser when you're searching flights to show you whether points or cash is the better deal.

Points Path takes the guesswork out of booking. It helps you instantly compare cash fares and award redemptions on Google Flights, showing you where the real value lies so you can make the best booking decision every time.

We talk trends in the award travel landscape, how Points Path focuses on simplicity to take the guesswork out of choosing flights, and why this tool deserves a place in your browser. Whether you're a casual traveler or a seasoned award booker, you'll also hear how its alert feature can track award prices and let you know when they drop — so you don't have to keep checking.

Julian shares how Points Path was designed to focus on simplicity, taking the guesswork out of choosing flights so you always know the best option. With more than 10 years of experience working with some of the most trusted names in the award travel space, Julian brings both insight and innovation to how we think about booking smarter.

Get full show notes and transcript: https://pointmetofirstclass.com/plan-award-flights-faster-with-points-path/

Want to shape the show? Take the Point Me To First Class listener survey here and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

139. Stack Shopping Portals and Card Offers for Bigger Rewards with Savewise Oct 27, 2025

Show notes

Do you ever find yourself opening multiple tabs, comparing shopping portal payouts, and trying to figure out which site is going to give you the most rewards for your online shopping — only to give up before you actually earn the points?

If that sounds familiar, today's episode is for you.

In this Streamline, Stack, and Save mini-series episode, I'm joined by Avneesh Kohli, founder of Savewise, a powerful tool that shows you exactly how to combine the best shopping portal payouts with card-linked offers — so you can maximize every online purchase without the hassle of manual tracking or endless research.

Savewise is a total game changer for award travelers who want to earn more points without wasting time. The platform automatically finds the best portal and card-linked combinations for each purchase, helping you get the highest payout possible — every time you shop online.

In this conversation, Avneesh and I talk about how Savewise works, why it's become one of my favorite online tools, and how it helps you earn more points with less effort. We also dive into how it fits into a broader points-earning strategy, why automation is key to long-term success, and how you can start using it right now — just in time for holiday shopping.

Whether you're new to the points world or a seasoned award traveler, this episode will help you make every purchase count.

Get full show notes and transcript: https://pointmetofirstclass.com/track-and-save-money-with-savewise/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here.

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